CA2261500C - Stable oxaliplatin solutions and their use in cytostatic antineoplastic treatment - Google Patents
Stable oxaliplatin solutions and their use in cytostatic antineoplastic treatment Download PDFInfo
- Publication number
- CA2261500C CA2261500C CA002261500A CA2261500A CA2261500C CA 2261500 C CA2261500 C CA 2261500C CA 002261500 A CA002261500 A CA 002261500A CA 2261500 A CA2261500 A CA 2261500A CA 2261500 C CA2261500 C CA 2261500C
- Authority
- CA
- Canada
- Prior art keywords
- oxaliplatin
- formulation according
- amount
- buffering agent
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 title claims abstract description 79
- 229960001756 oxaliplatin Drugs 0.000 title claims abstract description 79
- 239000000824 cytostatic agent Substances 0.000 title claims description 4
- 230000001085 cytostatic effect Effects 0.000 title claims description 4
- 230000000118 anti-neoplastic effect Effects 0.000 title claims 2
- 239000000203 mixture Substances 0.000 claims abstract description 100
- 238000009472 formulation Methods 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 9
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 75
- 239000006172 buffering agent Substances 0.000 claims description 24
- 235000006408 oxalic acid Nutrition 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- -1 alkali metal salt Chemical class 0.000 claims description 12
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 claims description 12
- 229940039790 sodium oxalate Drugs 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 230000001954 sterilising effect Effects 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 229940127557 pharmaceutical product Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 3
- 239000003708 ampul Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 15
- 239000000243 solution Substances 0.000 description 73
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 102100028735 Dachshund homolog 1 Human genes 0.000 description 23
- 101000915055 Homo sapiens Dachshund homolog 1 Proteins 0.000 description 23
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 239000012535 impurity Substances 0.000 description 16
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 10
- 229910052697 platinum Inorganic materials 0.000 description 9
- 239000000872 buffer Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 241000208167 Oxalis Species 0.000 description 4
- 235000016499 Oxalis corniculata Nutrition 0.000 description 4
- 239000012062 aqueous buffer Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229940034982 antineoplastic agent Drugs 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 230000002045 lasting effect Effects 0.000 description 3
- 229940039748 oxalate Drugs 0.000 description 3
- NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000003327 cancerostatic effect Effects 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000008176 lyophilized powder Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 150000003058 platinum compounds Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010061424 Anal cancer Diseases 0.000 description 1
- 208000007860 Anus Neoplasms Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- WAKVAVXIAXQHQT-UHFFFAOYSA-N [Na].[Na].[Na].[Na].[Na].[Na].[Na] Chemical compound [Na].[Na].[Na].[Na].[Na].[Na].[Na] WAKVAVXIAXQHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 201000011165 anus cancer Diseases 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000001120 cytoprotective effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 201000010175 gallbladder cancer Diseases 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 208000021267 infertility disease Diseases 0.000 description 1
- 229940025708 injectable product Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012792 lyophilization process Methods 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 210000004560 pineal gland Anatomy 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 201000002314 small intestine cancer Diseases 0.000 description 1
- 239000008227 sterile water for injection Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 206010044412 transitional cell carcinoma Diseases 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A61K31/282—Platinum compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9804013.2 | 1998-02-25 | ||
| GBGB9804013.2A GB9804013D0 (en) | 1998-02-25 | 1998-02-25 | Formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2261500A1 CA2261500A1 (en) | 1999-08-25 |
| CA2261500C true CA2261500C (en) | 2001-07-17 |
Family
ID=10827600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002261500A Expired - Lifetime CA2261500C (en) | 1998-02-25 | 1999-02-11 | Stable oxaliplatin solutions and their use in cytostatic antineoplastic treatment |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6306902B1 (cs) |
| EP (1) | EP0943331B1 (cs) |
| JP (1) | JP4430229B2 (cs) |
| KR (1) | KR20010041182A (cs) |
| CN (1) | CN1152718C (cs) |
| AR (1) | AR015524A1 (cs) |
| AT (1) | ATE202472T1 (cs) |
| AU (1) | AU757101B2 (cs) |
| BR (1) | BR9908273A (cs) |
| CA (1) | CA2261500C (cs) |
| CZ (1) | CZ302196B6 (cs) |
| DE (1) | DE69900162T2 (cs) |
| DK (1) | DK0943331T3 (cs) |
| ES (1) | ES2161085T3 (cs) |
| GB (1) | GB9804013D0 (cs) |
| GR (1) | GR3036646T3 (cs) |
| GT (1) | GT199900019A (cs) |
| HU (1) | HU224611B1 (cs) |
| IL (1) | IL137772A (cs) |
| MX (1) | MXPA00008195A (cs) |
| NO (1) | NO329900B1 (cs) |
| PL (1) | PL197948B1 (cs) |
| PT (1) | PT943331E (cs) |
| RU (1) | RU2207857C2 (cs) |
| UA (1) | UA70316C2 (cs) |
| WO (1) | WO1999043355A2 (cs) |
| ZA (1) | ZA991489B (cs) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9804013D0 (en) | 1998-02-25 | 1998-04-22 | Sanofi Sa | Formulations |
| BRPI9914508B8 (pt) * | 1998-10-14 | 2021-05-25 | Debiopharm Sa | bolsa flexível impermeável para uso médico contendo uma preparação farmacêutica de oxaliplatina sob a forma líquida |
| US7070796B1 (en) | 1999-08-30 | 2006-07-04 | Debiopharm S.A. | Pharmaceutically stable oxaliplatinum preparation for parenteral administration |
| KR100688217B1 (ko) * | 1999-08-30 | 2007-02-28 | 데비오 팜 소시에떼 아노님 | 비경구 투여용의 약학적으로 안정된 옥살리백금 약학제제 및 그 조제방법 |
| WO2002047725A2 (fr) * | 2000-12-12 | 2002-06-20 | Debiopharm S.A. | Preparation pharmaceutique d'oxaliplatine pour administration par voie parenterale et procede d'obtention de ladite preparation |
| PT1368022E (pt) | 2001-03-02 | 2007-10-01 | Debiopharm Sa | Utilização de um frasco em vidro que contém uma solução de oxaliplatina |
| WO2003004505A1 (en) | 2001-07-02 | 2003-01-16 | Debiopharm S.A. | Oxaliplatin active substance with a very low content of oxalic acid |
| US6476068B1 (en) * | 2001-12-06 | 2002-11-05 | Pharmacia Italia, S.P.A. | Platinum derivative pharmaceutical formulations |
| CA2388352A1 (en) * | 2002-05-31 | 2003-11-30 | Voiceage Corporation | A method and device for frequency-selective pitch enhancement of synthesized speed |
| DE10314377A1 (de) * | 2003-03-28 | 2004-10-07 | Stada Arzneimittel Ag | Gebrauchsfertige Oxaliplatin-Lösungen |
| US20050020556A1 (en) * | 2003-05-30 | 2005-01-27 | Kosan Biosciences, Inc. | Method for treating diseases using HSP90-inhibiting agents in combination with platinum coordination complexes |
| GB2441445B (en) * | 2003-08-28 | 2008-04-23 | Mayne Pharma Ltd | Acid containing oxaliplatin formulation |
| CN101022790A (zh) * | 2003-08-28 | 2007-08-22 | 梅恩医药有限公司 | 含有酸的奥沙利铂制剂 |
| JP2007504177A (ja) * | 2003-09-02 | 2007-03-01 | プリヴァ−ラケマ，エー．エス． | 医薬組成物、その製造方法及び治療上の使用 |
| CZ300795B6 (cs) * | 2003-09-02 | 2009-08-12 | Pliva-Lachema A. S. | Farmaceutická kompozice a zpusob její výroby |
| WO2005051966A1 (en) | 2003-11-25 | 2005-06-09 | Platco Technologies (Proprietary) Limited | Platinum(ii) complexes, preparation and use |
| PL1695991T3 (pl) * | 2003-12-10 | 2010-05-31 | Toudai Tlo Ltd | Koordynacyjny kompleks diaminocykloheksanu platyny (II) z blokowym kopolimerem zawierającym fragment poli(kwasu karboksylowego), oraz środek przeciw-nowotworowy zawierający ten kompleks |
| CN100471493C (zh) * | 2003-12-17 | 2009-03-25 | 梅比欧法姆股份有限公司 | 含有奥沙利铂的脂质体制剂 |
| WO2005102312A1 (en) * | 2004-04-27 | 2005-11-03 | Mayne Pharma Limited | Concentrated oxaliplatin solutions |
| NZ553044A (en) | 2004-09-01 | 2010-09-30 | Placto Technologies Proprietar | Preparations of platinum(II) complexes |
| US20060063720A1 (en) * | 2004-09-22 | 2006-03-23 | Edgar Schridde | Oxaliplatin solution concentrate |
| US20060063833A1 (en) * | 2004-09-22 | 2006-03-23 | Edgar Schridde | Ready-to-use oxaliplatin solutions |
| DE102004052877B4 (de) * | 2004-11-02 | 2008-06-19 | Ebewe Pharma Ges.M.B.H. Nfg.Kg | Stabile wässrige Formulierungen eines Platin-Derivats |
| DE102004063764A1 (de) * | 2004-12-29 | 2006-07-13 | Hexal Ag | Kunststoff-Flasche für Oxaliplatin |
| JP2006248978A (ja) | 2005-03-10 | 2006-09-21 | Mebiopharm Co Ltd | 新規なリポソーム製剤 |
| EP1879568B1 (en) * | 2005-03-28 | 2009-05-06 | Dabur Pharma Limited | Stable pharmaceutical compositions of platinum (ii) antitumour agents |
| EP1874290A1 (en) * | 2005-04-09 | 2008-01-09 | Vuab Pharma A. S. | A process for the preparation of an oxaliplatin preparation |
| RU2292210C1 (ru) * | 2005-05-03 | 2007-01-27 | Институт химии и химической технологии СО РАН (ИХХТ СО РАН) | Способ получения стерилизованной микрокристаллической цис-дихлородиамминплатины (ii) |
| DE102005038347A1 (de) * | 2005-08-11 | 2007-02-15 | Hexal Ag | Herstellung einer Oxaliplatin-Lösung und Behälter sowie Behälter-Set mit der Lösung |
| WO2007029268A2 (en) * | 2005-09-05 | 2007-03-15 | Dabur Pharma Limited | Stable oxaliplatin formulation |
| AU2007209099A1 (en) | 2006-01-30 | 2007-08-02 | Platco Technologies (Proprietary) Limited | Preparation of platinum (ll) complexes |
| KR100913063B1 (ko) | 2006-09-13 | 2009-08-21 | 주식회사유한양행 | 옥살리플라틴-함유 주사용 용액 |
| CA2675788A1 (en) * | 2007-01-22 | 2008-07-31 | Pliva - Lachema A.S. | Oxaliplatin pharmaceutical composition with alcoholic sugar-based buffer |
| RU2340347C2 (ru) * | 2007-01-24 | 2008-12-10 | Институт химии и химической технологии СО РАН (ИХХТ СО РАН) | Способ получения стерилизованной микрокристаллической соли цис-дихлороамминизопропиламинплатины (ii) |
| US20100267824A1 (en) * | 2007-11-12 | 2010-10-21 | Intas Pharmaceuticals Limited | Stable oxaliplatin composition for parenteral administration |
| US20090130017A1 (en) * | 2007-11-19 | 2009-05-21 | Searete Llc | Targeted short-lived drug delivery |
| WO2010056847A2 (en) * | 2008-11-13 | 2010-05-20 | Taigen Biotechnology Co., Ltd. | Lyophilization formulation |
| CN101461801B (zh) * | 2008-12-26 | 2013-05-15 | 辰欣药业股份有限公司 | 一种奥沙利铂药物组合物及其制备方法 |
| AU2010296180B2 (en) | 2009-09-21 | 2016-05-05 | Bio-Synectics, Inc | Oxaliplatin nanoparticles and method for preparing same |
| CN102274171A (zh) * | 2011-08-04 | 2011-12-14 | 上海希迪制药有限公司 | 一种奥沙利铂注射剂 |
| CN104523674B (zh) * | 2014-12-11 | 2017-10-24 | 广州市上为医药科技有限公司 | 一种以奥沙利铂为主药成分的注射用组合物 |
| KR101683635B1 (ko) * | 2014-12-29 | 2016-12-09 | 가천대학교 산학협력단 | 락테이트 금속염을 포함하는 암 치료용 약학 조성물 |
| CN104829653B (zh) * | 2015-05-06 | 2016-03-23 | 山东罗欣药业集团股份有限公司 | 一种奥沙利铂水合物晶体及其冻干粉针剂 |
| WO2019138379A1 (en) | 2018-01-12 | 2019-07-18 | Metimedi Pharmaceuticals Co., Ltd. | Methods of treating chronic inflammatory diseases |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6041077B2 (ja) * | 1976-09-06 | 1985-09-13 | 喜徳 喜谷 | １，２‐ジアミノシクロヘキサン異性体のシス白金（２）錯体 |
| PT93772A (pt) | 1989-04-17 | 1991-01-08 | Searle & Co | Processo para a preparacao de composicoes para o tratamento de neoplasias, contendo um agente anti-neoplastico, por exemplo doxorubicina e um agente protector para reduzir os efeitos secundarios, por exemplo carbetimer |
| US5214174A (en) | 1989-12-15 | 1993-05-25 | Tsumura & Co. | Platinum complex and anti-tumor agent comprising said complex as active ingredient |
| JPH04185601A (ja) * | 1990-11-20 | 1992-07-02 | Unitika Ltd | 白金抗癌剤徐放性製剤 |
| DE69233169T2 (de) | 1991-11-15 | 2004-05-27 | Smithkline Beecham Corp. | Cisplatin und Topotecan enthaltende Zusammensetzung als antitumor. |
| JPH0776230B2 (ja) * | 1992-01-13 | 1995-08-16 | 田中貴金属工業株式会社 | 白金化合物の製造方法 |
| JPH05238936A (ja) | 1992-02-27 | 1993-09-17 | Dainippon Pharmaceut Co Ltd | カルシトリオールの水性液剤 |
| JP2673331B2 (ja) * | 1993-01-12 | 1997-11-05 | 田中貴金属工業 株式会社 | 光学的に高純度なシス―オキザラート（トランス―１―１，２―シクロヘキサンジアミン）白金（▲ｉｉ▼） |
| JPH06287021A (ja) * | 1992-04-22 | 1994-10-11 | Tanaka Kikinzoku Kogyo Kk | 光学活性な白金錯化合物の光学的分割方法 |
| WO1994012193A1 (fr) * | 1992-11-24 | 1994-06-09 | Debiopharm S.A. | Combinaison de cisplatine avec l'oxaliplatine |
| JP3025602B2 (ja) * | 1993-05-21 | 2000-03-27 | デビオファーム エス．アー． | 光学的に高純度なシス−オキザラート（トランス−ｌ−１，２−シクロヘキサンジアミン）白金（ＩＩ）錯体の製造方法 |
| US5455270A (en) * | 1993-08-11 | 1995-10-03 | Bristol-Myers Squibb Co. | Stabilized solutions of platinum(II) antitumor agents |
| RU2148400C1 (ru) | 1994-08-08 | 2000-05-10 | Дебиофарм С.А. | Фармацевтически стабильный препарат оксалиплатины |
| EP1369116A1 (en) * | 1994-11-11 | 2003-12-10 | Debiopharm S.A. | Oxalatoplatin and 5-fluorouracil for combination therapy of cancer |
| FR2740686B1 (fr) * | 1995-11-03 | 1998-01-16 | Sanofi Sa | Formulation pharmaceutique lyophilisee stable |
| DK1308454T3 (da) | 1996-04-10 | 2005-08-01 | Debiopharm Sa | Fremgangsmåde til fremstilling af platinforbindelse |
| JPH09294809A (ja) | 1996-05-07 | 1997-11-18 | Terumo Corp | 薬液注入器具 |
| GB9804013D0 (en) | 1998-02-25 | 1998-04-22 | Sanofi Sa | Formulations |
-
1998
- 1998-02-25 GB GBGB9804013.2A patent/GB9804013D0/en not_active Ceased
-
1999
- 1999-02-11 GT GT199900019A patent/GT199900019A/es unknown
- 1999-02-11 CA CA002261500A patent/CA2261500C/en not_active Expired - Lifetime
- 1999-02-22 US US09/255,087 patent/US6306902B1/en not_active Expired - Lifetime
- 1999-02-24 AR ARP990100774A patent/AR015524A1/es active IP Right Grant
- 1999-02-24 ZA ZA9901489A patent/ZA991489B/xx unknown
- 1999-02-25 MX MXPA00008195A patent/MXPA00008195A/es active IP Right Grant
- 1999-02-25 DK DK99301412T patent/DK0943331T3/da active
- 1999-02-25 AT AT99301412T patent/ATE202472T1/de active
- 1999-02-25 KR KR1020007009239A patent/KR20010041182A/ko not_active Ceased
- 1999-02-25 CZ CZ20003089A patent/CZ302196B6/cs not_active IP Right Cessation
- 1999-02-25 JP JP2000533150A patent/JP4430229B2/ja not_active Expired - Lifetime
- 1999-02-25 CN CNB99803276XA patent/CN1152718C/zh not_active Expired - Lifetime
- 1999-02-25 PL PL343021A patent/PL197948B1/pl unknown
- 1999-02-25 RU RU2000121254/14A patent/RU2207857C2/ru active
- 1999-02-25 AU AU26324/99A patent/AU757101B2/en not_active Expired
- 1999-02-25 HU HU0103707A patent/HU224611B1/hu active IP Right Grant
- 1999-02-25 DE DE69900162T patent/DE69900162T2/de not_active Ceased
- 1999-02-25 UA UA2000095450A patent/UA70316C2/uk unknown
- 1999-02-25 PT PT99301412T patent/PT943331E/pt unknown
- 1999-02-25 ES ES99301412T patent/ES2161085T3/es not_active Expired - Lifetime
- 1999-02-25 BR BR9908273-0A patent/BR9908273A/pt not_active Application Discontinuation
- 1999-02-25 WO PCT/GB1999/000572 patent/WO1999043355A2/en not_active Application Discontinuation
- 1999-02-25 EP EP99301412A patent/EP0943331B1/en not_active Expired - Lifetime
-
2000
- 2000-08-09 IL IL137772A patent/IL137772A/en not_active IP Right Cessation
- 2000-08-24 NO NO20004240A patent/NO329900B1/no not_active IP Right Cessation
-
2001
- 2001-09-18 GR GR20010401504T patent/GR3036646T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2261500C (en) | Stable oxaliplatin solutions and their use in cytostatic antineoplastic treatment | |
| AU2002352105B2 (en) | Platinum derivative pharmaceutical formulations | |
| RU2148400C1 (ru) | Фармацевтически стабильный препарат оксалиплатины | |
| AU671605B2 (en) | Combination chemotherapy | |
| US20100093849A1 (en) | Oxaliplatin pharmaceutical composition with alcoholic sugar-based buffer | |
| CZ300664B6 (cs) | Sterilní kapalná farmaceutická kompozice a zpusob její výroby | |
| HK1036405B (en) | A stable oxaliplatin solution formulation and the preparation process thereof | |
| US20050176619A1 (en) | Antitumoral formulations of thioxanthenone | |
| CZ300665B6 (cs) | Sterilní kapalná farmaceutická kompozice a zpusob její výroby | |
| KR20080025004A (ko) | 옥살리플라틴-함유 주사용 용액 | |
| HK1072002B (en) | Platinum derivative pharmaceutical formulations | |
| AU2002319400A1 (en) | Antitumoral formulations of thioxanthenone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20190211 |